What does Matthew 11:16 mean?

Jesus begins to build a negative analogy about the generation of Israelites in His day. He uses a common Jewish phrase: "to what shall I compare" something? In this case, He compares His generation to children playing in the marketplace.

In all His analogies and metaphors, Jesus reflects a deep awareness of what is happening in the world around Him, including being tuned in to the games of children. He is aware that kids play "wedding" and "funeral" and sometimes complain when their peers don't join in. The point of the comparison will be to show that the people of Israel in His generation also complain that John the Baptist and Jesus are unwilling to play their "games" or meet their expectations about how the two of them should behave and speak.

This analogy will also speak to how fickle and inconsistent people can be when they resist the truth. The following verse will present two completely opposite complaints. This, however, is how many who reject God respond to Him. No matter what He shows them, or what they see, they simply demand the opposite.